Tangled In The Wind
by sofaritsalright
Summary: Jess and Rory left things on a bad note over a year ago, but now that they're both in Stars Hollow for a wedding, they try to rehash the past and figure out their next step.
1. Weight of the World

**A/N:** Hello, my loves! Long time no see. My sincerest apologies for being away for so long without new fics or updates, but after the revival, I couldn't necessarily see myself writing anymore Gilmore Girls fics. However, this changed in the past few months and I've been itching to write my two favorites once again. That being said, this is my attempt at re-writing the revival and ignoring (most of) canon because that's just what I'm best at. Please comment/favorite/review if you like it and want to see more of this story!

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Autumn in Stars Hollow was more beautiful than most places. It's where Rory Gilmore felt most at home; it's what made Stars Hollow home. Since graduating college, she'd lived in multiple places, but even winter in London and spring in New York couldn't compare to the warmth that her tiny Connecticut hometown could bring her. The moment her feet touched the ground outside of her mother's house, she could practically taste the hot cider she shared with Lane every year and taste the sweetness of the pumpkin pies from Weston's Bakery. Everything about this felt _right_. Rory took a moment to stretch her legs upon getting out of her cramped car — needless to say, a two-hour drive was not what she was used to after living in a big city, but she managed. As she stood there in the gravel driveway, she smiled at the scenery, feeling like a teenager all over again at the sights that hadn't changed over the years. Globes still littered Babette's lawn, the roof tiles of the Gilmore estate were still out of place (although Luke said he'd fix those when he had the time), and there was still the faint outline of four letters reading "GG+DF" in nail polish underneath the repainted porch. No matter how many times she'd tried to erase those hot pink letters, they were there to stay and by this point in her adulthood, she was okay with it.

She hoists her bag up onto her shoulder while walking up the stairs before tilting to the side, letting her hip open up the parted door for her. It was almost foreign to walk into a home that didn't have at least three locks on the doors. "Lucy, I'm home!" she announces, smiling at the freshly painted living room and walkway. While there was always something new to come home to, it was all the same. Lorelai was never one for change and Luke learned to accept it.

It only takes a few seconds for Lorelai to come rushing down the stairs in her sweatpants, looking as if she was in the middle of doing her makeup for the day. It was Rory's mistake - she did choose to come home at an unreasonably early hour (Lorelai's words). Before she can even make it down the stairs, Rory is there to greet her with open arms. "Oh, Ricky, I never thought you'd return." Lorelai smiles, gripping her daughter tight until Rory feigns choking sounds. "I missed you, kid."

"You know you could come visit _me_ every once in a while." Rory crosses her arms, giving her mother a soft smile. Lorelai visited when she could, but it wasn't enough. All the time in the world could never be enough to make up for the time they hadn't spent together in the last decade or so. She missed Lorelai dearly which is why they were constantly texting and calling each other when given time.

Lorelai tilts her head back and forth at the comment. "I could, but where's the fun in that? Broadway's entertaining, but its got nothing on Stars Hollow." To that, Rory couldn't disagree. Although New York was big, loud, and full of dramatics, it wasn't nearly as amusing as the townsfolk in her own town. "You've got a point there," Rory nods as the front door gets opened and closed.

"Coffee." A booming, yet monotone voice comes through the front door. Luke was a delight to see, but the coffee was somehow more welcomed. She takes it out of the carrier before taking a long, generous sip. God, she had missed this. "Good to see you again, Rory," Luke says as he lays a duffle bag on the floor next to the couch.

Baby blues eye up the plain, black luggage, realizing suddenly that it wasn't hers and it most likely didn't belong to her mother or soon-to-be official step-dad. It all hits her when she sees the tag on the zipper. "J.M." is written clearly in big, Sharpie letters on the white tag, leaving Rory's heart to leap... or jump... or drop. She isn't sure what it truly does, but she can feel it pound out of her chest. Any normal person would say this was a reaction to the third coffee of the morning, but after years of coffee consumption, she knew that this wasn't a caffeinated reaction. Although Luke and Lorelai were bantering back and forth rather loudly, she was focused enough to hear the door open once more and the shuffling of boots making its way towards the three.

"Jess," Rory says immediately, too taken back to say anything else. His presence shouldn't have been a shock — he was Luke's best man after all — but she stood there with large doe eyes, unable to greet him in any normal manner. It'd been well over a year since they last stood in front of each other, rambling on their goodbyes as tears streamed down Rory's rogued cheeks. For the most part, Rory thought she'd psyched herself up enough for this moment, but clearly, she was wrong.

That lopsided grin beams brightly at her as if no time had passed at all; as if their last words weren't some angry exchange and all was good between them. "I see your coffee addiction is still going strong." He wasn't much for greetings (or even goodbyes, for that matter) and that both irked and impressed Rory to no end. Every little quirk that made Jess Jess was both appealing and truly gutwrenching to the woman. They knew each other like the back of their hands... and perhaps that's what gave them their unruly end.

"It's a part of who we are," Lorelai pipes up after noticing that her daughter hadn't moved or even blinked since Jess walked in. "Who knew that you'd start sounding like Luke." Eyes dart over towards her fiancé, giving him a glare as she takes a sip of the coffee he had nicely brought over from the diner. Although he didn't approve of their so-called addiction, he didn't help any by practically pouring it down their throats whenever they asked.

Jess's hands raise, deeming him defenseless. "Luke judges, I only comment."

Rory finally clears her throat, still thinking of the words to say. For being a Gilmore and a writer, words seemed to flee her every time she saw Jess or was reminded of the very incident that made them part ways for good. "So, where will you be staying while you're here?" she inquires, praying that it's far away from her.

Jess shoves his hands in his pockets at the unexpected question before his gaze shoots to the floor. Luckily for both of them, Luke steps in just like Lorelai did earlier. "Plumbing's out in the old apartment above the diner. I told him he could crash on the couch." Lorelai nudges Luke in the side, causing him to jump slightly. "If that's alright with you, of course," he adds.

Rory nods slowly. "Yeah, yeah. That's fine." It wasn't. She felt like her turf was being invaded, but she was too nice to say otherwise.

"I told him I could get a room somewhere else," Jess adds, finally looking back up at her.

"I said it's fine." Her reiteration causes Jess to shift in his spot as he gives her a knowing look. He could read her like no other which was also a grand pain in the ass in Rory's mind. "I'm gonna go unpack," she announces, picking up one of her bags from the ground. "Thanks for the coffee, Luke." She doesn't wait for a response from anyone before shuffling towards her childhood bedroom, instead, she chooses to get away from it all before the past came back up like bile in her stomach. Throwing her bags on the floor and shutting the door loudly behind her, she takes a deep breath and throws herself face-down on the bed, not noticing the fact that Paul Anka was tilting his head from his bed in the corner of the room. Instead, she was focused on the mere fact that once her head was hanging over the side of the twin sized bed, her gaze landed on a stray book.

 _"Then I'll leave you this last little trick," Jess told her, presenting her with an Allen Ginsberg book. "You bought a copy? I told you I'd lend you mine," she said upon seeing the front cover. "It is yours," he stated, not even sounding somewhat guilty. "You stole my book." Rory stopped, giving him a disappointed glare. "Nope, borrowed it." He had downright stolen her book, but at least he gave it back, even after defacing the inside with notes in the margins._

Rory studies the cover as the memories rush over her. Howl. It's small, yet it holds the weight of the world. Books still meant everything to the girl and there were quite a few that she holds near and dear to her heart; it just so happened that this was one of them. She wouldn't admit it to anyone, but often throughout the years, when she was thinking about Jess, she pulled out her nearest copy and read through it once again. As the author wrote in said book, "the weight of the world is love" and after meeting Jess, she knew that to be true.

It feels like she stares at the book of poetry for an eternity, but Paul Anka's whimpering pulls her out of the world she was dizzily floating around in. Eyes slowly shoot his way and Rory just sighs. "It's going to be a long four days," she tells him. "I guess we're in it for the long haul whether we like it or not, aren't we?" Rory knows full well that he wasn't going to respond with anything other than a stare in her direction and it left her feeling like Lorelai, but right now she had no other choice than to talk to a dog. Rory gingerly picks the book up off the floor, ready to skim through the pages once again, only to see what seventeen-year-old Jess had running through his mind at the time he sloppily wrote notes in the book margins. A finger grazes his words as she wonders where in their story they went wrong. Maybe they were always destined for some sort of goodbye, but that never made sense to her. No matter how hard they tried, they always seemed to get it wrong and it drove her insane as she pondered over the past, carefully trying to pinpoint why they couldn't just make it work for once.

It's when she's lost in her own thoughts once again that she hears her phone buzzing in her purse. She'd been waiting for Lane's response to her being home, but as soon as she pulled it out to look at the screen, all of that hope was flushed out of her system, leaving her with a nauseous feeling.

 _ **From Jess:**_ _The Inn is booked for the wedding, but I'm going to try the Motel 6 place in Hartford. I'll be out of your hair soon._

Before she even has the chance to process or even response, it dings once again.

 _ **From Jess:** Should we at least talk about this?_

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 **A/N 2:** So this was longer than most of my first chapters on fics, but I got carried away. I know my writing's a little rusty these days, but please let me know if you want more of this story. I'm kind of excited about it at this point and have an idea of what's to come. x


	2. I Watched It Begin Again

**A/N:** I know it's only been a day since the first chapter, but I'm really into this story so far. Thank you all for the first few followers, favorites, and reviews. You guys are truly the best. I'm gonna do my best to fix the mess that is Rory and Jess, but it may be a slow burn from here on out. Without further ado, here's a nice little flashback to start where the original series left off! And just so you all know, I will be expanding on both of the timelines here, as well as adding a few more in the future so we can get a glimpse at what lead them to the modern day tension. Please continue to be babes and let me know how you're feeling about this fic so far! xx

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 **JULY 4, 2007**

Most of the time Philadelphia wasn't where Jess's heart was, but he remained put until he had the money (or patience) to move. Where he was going, he didn't know. Wherever the wind would take him or whatever Bukowski would've done in a time that he was stuck in a mundane rut that kept him from going anywhere in this too-big world. For Jess, it was often that his mind drifted back to Rory. It'd been almost two years since the last time they'd come face-to-face and sometimes when his mind wandered off, he repeats every step and every word that happened that night. Since then, he'd been getting steady updates from Luke and sometimes even Liz, although he was sure they were both tired of him trying to subtly bring her up in conversations every now and then. As much as he hated Stars Hollow and everything that came along with it, he wishes he would've stayed. If he had, maybe things would've been different now, but at the tender, broken age of eighteen, making bad decisions was his forte. He could rattle off a whole laundry list of horrible mistakes he'd made that led him here, but what was the use in doing that? It was over and done with now, as much as he regretted it.

Now, he wasn't one for politics and tried to stay as far away from them as possible, but he'd been following Obama's campaign trail for the past year. Knowing that Rory was right there alongside the media circus was something that made him quite proud. _I'm going to be a journalist_ , she once told him. _I'm sure you'll do it. You will. I promise._ Somehow, someway, Jess made good on that promise - or prediction - whatever you want to call it. After trying (and succeeding) to get Rory back in school, he had every ounce of faith that she'd eventually become a journalist. Although this wasn't exactly an overseas correspondence job, being a political reporter right out of college wasn't too bad. Because of this, Jess now followed Obama's campaign closely, always waiting to read something by the author Rory Gilmore (sometimes written out as _Lorelai Gilmore_ , which always made Jess snicker at the thought of the real Lorelai writing anything political).

In fact, he'd followed Obama's trail closely enough to know that tomorrow night he'd be gracing Philadelphia with his presence and alongside him would be the one and only Rory Gilmore. All day he'd been itching to text or call, but he wasn't sure the girl would be too willing to see them after their last encounter left her cheating on her douchebag ex-boyfriend and his subtle way of saying that he still loved her. Maybe she'd forgotten all about him at this point. Who knows. After careful deliberation, he pulled out an old Post-It note that he kept lodged in a battered copy of A Farewell To Arms by the author Ernest Hemingway, whom Rory often bashed. He appreciated her opinion on his favorite books, but it was a stab in the heart to hear that he wasn't the girls' cup of tea. As he flipped through the pages to find the yellow note, he wondered if getting in touch with her was even a good idea in the first place. However, that mindset quickly changed the moment he saw the line that the note was right next to. " _Life isn't hard to manage when you've got nothing to lose_." Ernest and his lovely words were somehow reaching out to Jess even though the author lie deep in his grave.

A hand snaked into his coat pocket to dig out his phone; it was a simple flip-phone, probably the fifteenth one he had in the past two years. It drove everyone insane that he changed his number so often, but hey, what was the point in these stupid things anyway? It wasn't worth it; he'd end up being bothered by people who he couldn't handle if he didn't get a new number every now and then.

It took him a minute to compose his message but finally landed on one that seemed okay enough to send.

 **TO: RORY**  
 _Way to go, Gilmore. Soon you'll be kicking Maureen Dowd from her throne._

 **FROM: RORY**  
 _I know it's you, Logan. Stop texting me._

Well, that didn't go as planned. Jess's heart dropped and he almost didn't want to pick it up. How the hell it didn't come across Jess-like enough was beyond him. He was ready to give up, he decided to give it one more bitter attempt.

 **TO: RORY**  
 _Hate to break it to you, but you've got the wrong ex._

 **FROM: RORY**  
 _...Jess?_

 **TO: RORY**  
 _Who else would reference Maureen Dowd?_

There was a pause in the texts, making Jess extremely nervous. He wasn't one for letting nerves get to him - in fact, even when it came to relationships, he was usually absent-minded and hard to read. Anxiety wasn't his thing... until it came to Rory. How was it that he couldn't just let her go?

The more time passed, he was ready to throw in the towel. Until it started to ring, of course. He glanced at that Stars Hollow area code he had just entered into his phone only thirty minutes ago.

"I'm going to be very hurt if you meant to call a different ex," he said with a grin upon answering.

" _Forgive me for not recognizing the number. You do realize you've had about a million numbers since the last time we spoke, don't you? Only a drug dealer goes through that many numbers in a short span of time._ "

The grin spread at the realization that she'd been keeping track of him as well. "You've had my number all this time and didn't attempt to call me?"

For a second, Rory goes quiet and he realizes that she's smiling too. He can almost hear it on the other side of the phone call. It was typical Rory fashion to completely fall silent once he zoned in on one little part of what she was saying. " _Maybe I have, but it's not like you'd know anyway._ "

"Touché." He nods, completely defeated as he leans against the stairwell of Truncheon. "So, I see here that you and the possible 44th President are in Philly."

" _If you're calling to meet Barak, you're gonna have to be put on a long waiting list_."

"Barak? You're on a first name basis?"

" _I have spent eight months with him, you know_."

"I know, I've been doing my homework. You have too apparently. The writing's looking good, Gilmore."

" _And what about your writing? Anything good coming my way soon?_ "

"We'll see," he shrugs, not wanting to admit that his muse had long burned out since his last piece of crap novel. "How about we talk about it over dinner?"

The line goes silent once again and he can only hope that he didn't step out of line. " _I could eat,_ " she finally says.

"So I've been told," he snorts. "You've heard of Johnny's Hots? Best cheesesteak in all of Philadelphia. I guarantee it."

" _How's seven o'clock sound?_ "

"I'll see you there."

 **MODERN DAY**

Jess tried retracing his steps to where they first began again, to figure out where they went wrong. He'd go back to the very beginning, to him first stepping foot in the Gilmore house, but that was already said and done. That was chapter one through three of the Rory and Jess saga and he knew how that ended. Once Lorelai went back upstairs to finish her makeup and Luke headed back to the diner, Jess threw himself down on the couch to search for some sort of motel nearby. The Inn was already booked for the weekend, leaving him stranded. It took him a second to remember that Stars Hollow was small enough to get away with not having anywhere else to stay. God, at this point, even a Bed and Breakfast would do. Anything to take the tension off of them would've done it. He paused to think over his options while tapping his phone against his thigh, considering heading over to Hartford. It was 22 miles, but perhaps it was worth it just to get out of her hair. He also mulled over going to knock on the girl's old bedroom door to figure out what was going through her mind. That might've caused a few issues. Instead, he unlocked his phone and pulled up her number.

 **TO: RORY**  
 _The Inn is booked for the wedding, but I'm going to try a Motel 6 in Hartford. I'll be out of your hair soon._

 **TO: RORY**  
 _Should we at least talk about this?_

He waited for that stupid grey text bubble to pop up and give him an answer, but after a few minutes, it never came, leaving him to throw his head back in frustration. She was good at keeping him waiting in suspense, that was for sure. Lucky enough for him, her door slowly creaked open and she came shuffling out with her arms crossed. "I heard that Motel 6 has bedbugs," she says quietly, keeping her distance.

"Don't they all?" Jess asks, cautiously turning his head to look her way. He hadn't really looked her over when he came inside earlier, but now that his eyes were on her, he couldn't pull his gaze away. Sometimes when she was in his presence, he felt like a lovesick teenager all over again and could feel it by the way his facial features positioned - a reaction only one girl could get out of him. "I'd say it's pretty much a gamble." Not one that he was ready to take, honestly.

Fingers tap on her thin arms as she bites down on her bottom lip, waiting for any words that come to mind. It's just then that Jess realizes she looks anxiety-riddled and a tad defeated. As her head raises, she narrows her eyes carefully, looking like a scared doe that may just run off from fear. "Wanna go to the bridge?"

Chestnut eyes widen at her words, leaving him momentarily speechless. He was waiting for the words good luck on the motel or something along those lines, but suggesting they meet up at a place that held the most history between them was a step in the right direction. "As long as you don't pull a Luke and push me in the lake, I'm down."

By the way she's fighting the grin on her lips, he can tell that he at least said something right. "I can't promise anything, but I'll try not to. Although, I have heard that pushing someone in is cathartic."

 _Wanna push me in the lake? It's cathartic, I hear. Any attempt to snap Rory out of a mood was his goal from the very beginning. Maybe in a little bit, she responded, almost sounding serious._

"Mm, whoever told you that is a liar." He stands up from his comfortable position on the couch and heads towards the door, soon realizing that she wasn't following behind her.

"What are you doing?" she asks as soon as he turns to look over his shoulder.

Brows knit together in confusion as he shakes his head ever-so-slightly. "I thought we were going to the lake."

"I didn't mean right now."

"Now's as good of a time as any," he sighs. "It's not like either of us have anything else going on."

Rory takes a moment to ponder it before picking up her feet once again and sliding past him, heading out the door in a haste. "Can I at least get coffee first?"

Some time and hard feelings may have put a barrier between the two, but no matter what, she was still the same old Rory.


End file.
